Electrodepositable coating composition

a coating composition and electrode technology, applied in coatings, transportation and packaging, cosmonautic vehicles, etc., can solve the problems of unstable cured film, film resulting from hydroxyl functional phosphated epoxy resin not retaining film integrity,

Pending Publication Date: 2021-09-16
PRC DE SOTO INT INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The phosphated epoxy resin-based coating composition cures effectively at low temperatures and demonstrates improved hydrolytic stability, preventing degradation from water exposure and extending the coating's durability.

Problems solved by technology

However, the film resulting from the hydroxyl functional phosphated epoxy resin did not retain its film integrity after hydrolytic stability testing.
Without intending to be bound by any theory, it is believed that the instability of the cured film is due to the hydrolytically unstable nature of the hydroxyl-melamine bond.

Method used

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  • Electrodepositable coating composition
  • Electrodepositable coating composition
  • Electrodepositable coating composition

Examples

Experimental program
Comparison scheme
Effect test

example 1

on of an Aqueous Resinous Dispersion of a Hydroxyl-Functional Phosphated Epoxy Resin

[0140]Example 1A: A general procedure for making an aqueous resinous dispersion of a hydroxyl-functional phosphated epoxy resin was performed as follows:

Charge #MaterialAmount (g)1Bisphenol-A Diglycidyl Ether141.42Bisphenol-A45.53Butyl CELLOSOLVE114.142-Ethyl-1-hexanol21.25Ethyltriphenylphosphonium Bromide0.16Ektasolve EEH220.5785% Phosphoric Acid5.58Phenylphosphonic Acid3.39Ektasolve EEH0.910Deionized water9.611Diisopropanolamine15.612Cymel 1130370.213Deionized water138.114Deionized water247.812-Butoxyethanol available from Dow Chemical Company2Ethylene glycol 2-ethylhexyl ether available from Eastman Chemical Company3Cymel 1130 a methylated / n-butylated melamine-formaldehyde crosslinker available from Allnex (98% ± 2% non-volatile content)

[0141]Charges 1-5 were added to a flask set up for total reflux with stirring under nitrogen and heated to 130° C. and allowed to exotherm to 160° C. The mixture w...

example 2

on of a Carbamate-Functional Oligomer

[0148]A reaction schematic and general procedure for making a carbamate-functional oligomer (hydroxypropylcarbamate fully-capped hexamethylene diisocyanate trimer) was performed as follows:

Charge #MaterialAmount (g)1Hexamethylene Diisocyanate Trimer1970.02Methyl isobutyl ketone362.43Dibutyltindilaurate1.64Carbalink HPC (95% solids)2639.41Available as Desmodur N 3300 from Covestro2Hydroxypropylcarbamate commercially available from Huntsman

[0149]Charges 1-3 were added to a flask set up for total reflux with stirring under nitrogen. The mixture was heated to a temperature of 60° C. Charge 4 was added over 2 hours through an addition funnel while the resulting exotherm was maintained under 60° C. After 2 hours, the mixture revealed no residual isocyanate peak by IR (2200-2300 cm−1). The mixture was then cooled to 40° C. and poured out. Final solids were 84.2%. Final molecular weight as determined by GPC (Mz) was 2,999.

example 3

on of an Aqueous Resinous Dispersion of a Hydroxyl-Functional Phosphated Epoxy Resin and Carbamate-Functional Oligomer

[0150]Example 3A: A general procedure for making an aqueous resinous dispersion of a hydroxyl-functional phosphated epoxy resin and the carbamate-functional oligomer of Example 2 was performed as follows:

Charge #MaterialAmount (g)1Bisphenol-A Diglycidyl Ether184.42Bisphenol-A59.43Butyl carbitol formal7.54Ethyltriphenylphosphonium Bromide0.25Methyl isobutyl ketone19.56Ektasolve EEH41.47Butyl CELLOSOLVE37.382-Ethyl-1-hexanol49.7985% Phosphoric Acid14.610Phenylphosphonic Acid12.711Ektasolve EEH4.112Deionized water31.013Diisopropanolamine49.614Cymel 1130106.215Carbamate functional oligomer of Example 2336.316Deionized water358.617Deionized water532.4

[0151]Charges 1-4 were added to a flask set up for total reflux with stirring under nitrogen and heated to 130° C. and allowed to exotherm to 160° C. The mixture was held at 160° C. for 1 hour. After 1 hour, charge 5 was adde...

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Abstract

The present invention is directed to a phosphated epoxy resin comprising at least one terminal group comprising a phosphorous atom covalently bonded to the re sin by a carbon-phosphorous bond or by a phosphoester linkage; and at least one carbamate functional group. The present invention is also directed towards aqueous resinous dispersions comprising the phosphated epoxy resin, methods of coating a substrate, coated substrates, and methods of making a phosphated epoxy resin.

Description

FIELD OF THE INVENTION[0001]The present invention is directed towards a phosphated epoxy resin, aqueous dispersions of said phosphated epoxy resin, electrodepositable coating compositions containing said phosphated epoxy resin, coated substrates, methods of coating substrates, and methods of making a phosphated epoxy resin.BACKGROUND INFORMATION[0002]Electrodeposition as a coating application method involves the deposition of a film-forming composition onto a conductive substrate under the influence of an applied electrical potential. Electrodeposition has gained popularity in the coatings industry because it provides higher paint utilization, outstanding corrosion resistance, and low environmental contamination as compared with non-electrophoretic coating methods. Some coatings formed from electrodepositable coating compositions have lacked stability to hydrolysis resulting in degradation of the coating film from exposure to water. Other coatings formed from electrodepositable coat...

Claims

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Application Information

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Patent Type & AuthorityApplications(United States)
IPC IPC(8): C09D163/00C08K5/205C08K5/3492C08K5/521C08L63/00B64G1/22
CPCC09D163/00C08K5/205C08K5/3492C08L2201/54C08L63/00B64G1/226C08K5/521C09D5/4434C09D5/4442C08G18/792C08G18/3825C08G18/246C08L75/04C09D175/04
InventorDACKO, CHRISTOPHER A.MAYO, MICHAEL A.MCCOLLUM, GREGORY J.PEFFER, ROBIN M.LEE, SE RYEON
OwnerPRC DE SOTO INT INC